[(E)-(3S,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-1,3,7-trimethyl-2-oxo-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester

Base Information

Chemical Name:[(E)-(3S,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-1,3,7-trimethyl-2-oxo-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester
CAS No.:544429-34-7
Molecular Formula:C₃₂H₅₉O₇PSi₂
Molecular Weight:642.961
Hs Code.:

[(E)-(3S,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-1,3,7-trimethyl-2-oxo-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester

Synonyms:[(E)-(3S,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-1,3,7-trimethyl-2-oxo-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester

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Chemical Property of [(E)-(3S,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-1,3,7-trimethyl-2-oxo-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester

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Technology Process of [(E)-(3S,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-1,3,7-trimethyl-2-oxo-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester

There total 16 articles about [(E)-(3S,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-1,3,7-trimethyl-2-oxo-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

: 544429-70-1
[(E)-(3R,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1,3,7-trimethyl-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester

: 544429-34-7
[(E)-(3S,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-1,3,7-trimethyl-2-oxo-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jo034011x

Reference yield:

: 102191-92-4
tert-butyldimethylsiloxyacetaldehyde

: 544429-34-7
[(E)-(3S,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-1,3,7-trimethyl-2-oxo-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 84 percent / benzene / 48 h / 0 - 20 °C

2.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 78 percent / tetrahydrofuran / 0.08 h

3.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH₂Cl₂ / 20 h / -20 °C

3.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

4.1: 76 percent / TfOH

5.1: DIBAL-H

6.1: dibutylboron triflate; diisopropylethylamine / CH₂Cl₂ / 0.25 h / 0 °C

6.2: CH₂Cl₂ / 3 h / -78 °C

6.3: 89 percent / sodium acetate; hydrogen peroxide / methanol; CH₂Cl₂; H₂O / 1.5 h / 0 °C

7.1: 95 percent / trimethylaluminum / hexane; tetrahydrofuran / 0 - 20 °C

8.1: 100 percent / triethylamine / CH₂Cl₂ / 15 h / Heating

9.1: 93 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 0.75 h / -78 °C

10.1: tert-butyllithium / tetrahydrofuran; pentane / 0.75 h / -78 °C

10.2: 89 percent / tetrahydrofuran; pentane / 0.25 h / -78 °C

11.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; toluene; pentane; benzene; 1.1: Wittig olefination;
DOI:10.1021/jo034011x

Reference yield:

: 132835-15-5
(Z)-1,4-bis(tert-butyldimethylsilanyloxy)but-2-ene

: 544429-34-7
[(E)-(3S,4R,6S)-6-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-1,3,7-trimethyl-2-oxo-4-trimethylsilanyloxy-non-7-enyl]-phosphonic acid diethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 100 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

2.1: 84 percent / benzene / 48 h / 0 - 20 °C

3.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C

3.2: 78 percent / tetrahydrofuran / 0.08 h

4.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH₂Cl₂ / 20 h / -20 °C

4.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

5.1: 76 percent / TfOH

6.1: DIBAL-H

7.1: dibutylboron triflate; diisopropylethylamine / CH₂Cl₂ / 0.25 h / 0 °C

7.2: CH₂Cl₂ / 3 h / -78 °C

7.3: 89 percent / sodium acetate; hydrogen peroxide / methanol; CH₂Cl₂; H₂O / 1.5 h / 0 °C

8.1: 95 percent / trimethylaluminum / hexane; tetrahydrofuran / 0 - 20 °C

9.1: 100 percent / triethylamine / CH₂Cl₂ / 15 h / Heating

10.1: 93 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 0.75 h / -78 °C

11.1: tert-butyllithium / tetrahydrofuran; pentane / 0.75 h / -78 °C

11.2: 89 percent / tetrahydrofuran; pentane / 0.25 h / -78 °C

12.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; toluene; pentane; benzene; 2.1: Wittig olefination;
DOI:10.1021/jo034011x